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While the driving portion of your proposed trip could be completed in three to three and a half days, by the time you add in a stopover on the way to, and at least a day, in New York and a couple of days wandering through the many sights and small towns of New England, your time will be pretty well taken up. Still it's not impossible, but you probably should consider cutting back a bit around the edges of this trip.

Since you plan on taking your time getting to New York, I'd suggest that you head down through Letchworth and Watkins Glenn State Parks on the first day and spend the night around Corning (half way to NYC). Then on Day 2 use I-88/I-81/I-380/I-80 to Stroudsburg, PA and explore the Delaware Water Gap National Recreation Area before heading into New York.

As for the rest of your trip, after whatever time you plan to spend in New York, I think you have a decision to make. To be sure, I have enjoyed my times on Cape Cod, but those have almost all been during 'off' or at worst 'shoulder' season. The thought of fighting traffic onto, around and off of the Cape at the height of summer tourist season is not my idea of fun. I would suggest that instead, for this trip, you forego Cape Cod and head directly for Boston from New York. That's a relatively short drive and will leave you a good half day in Boston if you leave New York relatively early in the morning - but then that means you'll be in New York's rush hour traffic. If you want a bit of picturesque New England seacoast, you could then go from Boston out onto Cape Ann northeast of the city, with Rockport and Halibut Point State Park as two worthwhile destinations.

From there it's a relatively quick and easy matter to drive up MA-133 and MA-1A to Plum Island, Newburyport and ultimately (US-1 or I-95) Portsmouth, NH and Portland, ME. There are far too many great sites in New England to list here, so I will simply direct you to this discussion of some of the best. But my main recommendation would be that you generally try to cross northern New England aiming for a re-entry into Canada around Cornwall so that you can return to Toronto via the Thousand Islands region and the northern shore of Lake Ontario.

AZBuck